2,4,6,8-tetrahydroxypyrimidine-[5,4-d]pyrimidine
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
Stage #1: 2,4,6,8-tetrahydroxypyrimidine-[5,4-d]pyrimidine With thionyl chloride In 1,4-dioxane for 1h; Stage #2: With N,N-dimethyl-formamide In 1,4-dioxane for 1.5h; Darkness; | 88.59% |
With phosphorus pentachloride; trichlorophosphate at 145℃; for 25.5h; | 37% |
With chlorine; trichlorophosphate; phosphorus trichloride at 110℃; for 24h; |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
With phosphorus pentachloride; trichlorophosphate for 15h; Heating; | 51% |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
Stage #1: 1,5-dihydropyrimido[5,4-d]pyrimidine-2,4,6,8-(3H,7H)-tetrone With sodium hydroxide for 0.333333h; Heating; Stage #2: With phosphorus pentachloride; trichlorophosphate for 8h; Heating; | 39% |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
With phosphorus pentachloride; trichlorophosphate | |
With phosphorus pentachloride; trichlorophosphate |
5-amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: aq. ammonium chloride / 1 h / 140 - 210 °C 1.2: 73 percent / aq. NaOH / Heating 2.1: 51 percent / POCl3; PCl5 / 15 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water / 4 h / 100 °C 2.1: thionyl chloride / 1,4-dioxane / 1 h 2.2: 1.5 h / Darkness View Scheme |
5-aminoorotic acid
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N-benzyl-N,N,N-triethylammonium chloride; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol / 9 h / 150 - 160 °C 2: phosphorus pentachloride; trichlorophosphate / 25.5 h / 145 °C View Scheme |
6-Methyluracil
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: 2,2'-azobis(isobutyronitrile); cobalt(II) acetate; acetic acid; oxygen / 15 h / 80 °C 2.1: sodium hydroxide / water / 3 h 2.2: 25 - 45 °C / Inert atmosphere 3.1: copper; hydrogenchloride / water / 13 h / 40 °C / Inert atmosphere 4.1: sodium hydroxide / water / 4 h / 100 °C 5.1: thionyl chloride / 1,4-dioxane / 1 h 5.2: 1.5 h / Darkness View Scheme | |
Multi-step reaction with 5 steps 1.1: sodium hydroxide; water; oxygen / 95 °C 2.1: nitric acid; sulfuric acid / 1 h / 10 - 30 °C 3.1: sodium dithionite / water / 0.5 h / 35 °C 4.1: 0.33 h / 100 °C 4.2: 1 h / 90 - 100 °C 4.3: 0.5 h / 60 °C / pH 4 5.1: trichlorophosphate; phosphorus trichloride; chlorine / 24 h / 110 °C View Scheme |
orotic acid
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium hydroxide / water / 3 h 1.2: 25 - 45 °C / Inert atmosphere 2.1: copper; hydrogenchloride / water / 13 h / 40 °C / Inert atmosphere 3.1: sodium hydroxide / water / 4 h / 100 °C 4.1: thionyl chloride / 1,4-dioxane / 1 h 4.2: 1.5 h / Darkness View Scheme |
5-nitroorotic acid
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: copper; hydrogenchloride / water / 13 h / 40 °C / Inert atmosphere 2.1: sodium hydroxide / water / 4 h / 100 °C 3.1: thionyl chloride / 1,4-dioxane / 1 h 3.2: 1.5 h / Darkness View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium dithionite / water / 0.5 h / 35 °C 2.1: 0.33 h / 100 °C 2.2: 1 h / 90 - 100 °C 2.3: 0.5 h / 60 °C / pH 4 3.1: trichlorophosphate; phosphorus trichloride; chlorine / 24 h / 110 °C View Scheme |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
With hydrogenchloride In water for 24h; Reflux; | 105 g |
orotic acid sodium salt
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: nitric acid; sulfuric acid / 1 h / 10 - 30 °C 2.1: sodium dithionite / water / 0.5 h / 35 °C 3.1: 0.33 h / 100 °C 3.2: 1 h / 90 - 100 °C 3.3: 0.5 h / 60 °C / pH 4 4.1: trichlorophosphate; phosphorus trichloride; chlorine / 24 h / 110 °C View Scheme |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
With phosphorus derivatives In N,N-dimethyl-formamide at 106 - 150℃; for 6h; |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
4-methoxy-benzylamine
4,8-bis(benzylamino)-2,6-dichloropyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran at 20℃; for 1h; | 98% |
propylamine
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; for 1h; | 97% |
In tetrahydrofuran at 0 - 5℃; for 0.333333h; |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
propan-1-ol-3-amine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -78 - 20℃; for 0.5h; | 97% |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
methylamine
2,6-dichloro-N4,N8-dimethyl-pyrimido[5,4-d]pyrimidine-4,8-diamine
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; for 2h; | 96% |
In tetrahydrofuran at 0 - 5℃; for 0.333333h; | |
In tetrahydrofuran at 0 - 20℃; for 1h; Concentration; Temperature; |
piperidine
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
2,6-dichloro-4,8-bis(piperidin-1-yl)pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
With copper(l) iodide; caesium carbonate In nitrobenzene at 180℃; for 16h; Inert atmosphere; | 95% |
In tetrahydrofuran at 25℃; | 93% |
Substitution; | |
In tetrahydrofuran at 0 - 5℃; for 0.333333h; | |
In tetrachloromethane; acetone at 30℃; for 1h; |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
benzylamine
4,8-bis(benzylamino)-2,6-dichloropyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran at 25℃; | 93% |
With potassium carbonate In tetrahydrofuran at 25℃; for 0.333333h; | 69% |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
4-methoxy-benzylamine
2,6-dichloro-4,8-di-(4'-methoxybenzylamino)pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran at 25℃; | 93% |
propylamine
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -78℃; for 0.833333h; | 93% |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
ethylamine
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; for 2h; | 92% |
In tetrahydrofuran at 0 - 20℃; for 1h; | 88% |
In tetrahydrofuran at 0 - 5℃; for 0.333333h; |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
1-Amino-2-methyl-propan-2-ol
Conditions | Yield |
---|---|
Stage #1: 2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine; 1-Amino-2-methyl-propan-2-ol In tetrahydrofuran at -78℃; for 0.5h; Stage #2: With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -78℃; for 0.5h; | 92% |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
1-amino-2-propene
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; for 2h; | 91% |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
With water In tetrahydrofuran at 20℃; for 24h; | 91% |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
ethanolamine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -78℃; for 2h; | 88% |
n-Octylamine
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
2,6-dichloro-4,8-bis(N-octylamino)pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
In chloroform for 0.5h; cooling; | 87% |
In chloroform at 10℃; for 0.833333h; | 86% |
4-methoxy-N-methylbenzylamine
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
2,6-dichloro-4,8-di-(N-4'-methoxybenzyl-N-methylamino)pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran at 25℃; | 87% |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
dibenzylamine
2,6-dichloro-4,8-bis-(dibenzylamino)pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran at 25℃; | 87% |
In tetrahydrofuran at 0 - 5℃; for 0.333333h; |
n-Dodecylamine
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
In chloroform at 10℃; | 86% |
In chloroform cooling; | 86% |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
3,4-dimethoxybenzylamine
2,6-dichloro-N4,N8-bis(3,4-dimethoxybenzyl)pyrimido[5,4-d]pyrimidine-4,8-diamine
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran at 25℃; | 83% |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
p-Trifluoromethylbenzylamine
2,6-dichloro-4,8-di-(4'-trifluoromethylbenzylamino)pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran at 25℃; | 81% |
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 120℃; for 3h; | 77% |
[2-fluoro-4-(methylthio)phenyl]amine
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
Stage #1: [2-fluoro-4-(methylthio)phenyl]amine; 2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine In tetrahydrofuran; water at 0 - 20℃; for 1h; Stage #2: With 3-chloro-benzenecarboperoxoic acid In tetrahydrofuran; dichloromethane; water at 0 - 20℃; | 77% |
N-methylhexanamine
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
In chloroform cooling; | 76% |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
cyclopropanemethylamine
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; for 3h; | 76% |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
N-benzyl-N-(3,4-dimethoxybenzyl)amine
2,6-dichloro-4,8-di-(N-benzyl-N-3',4'-dimethoxybenzylamino)pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran at 25℃; | 74% |
With potassium carbonate In tetrahydrofuran at 25℃; for 1h; Substitution; |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
2,2'-iminobis[ethanol]
2,6-dichloro-4,8-bis-(diethanoloamino)pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
In tetrahydrofuran at 25℃; | 74% |
4-cyano-2-fluoroaniline
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; for 1h; | 74% |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
benzylamine
4-benzylamino-2,6,8-trichloropyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran for 0.166667h; | 72% |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
benzyl-methyl-amine
2,6-dichloro-4,8-di-(N-benzyl-N-methylamino)pyrimido[5,4-d]pyrimidine
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran at 25℃; | 72% |
2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine
(R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol
Conditions | Yield |
---|---|
Stage #1: (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol With sodium hydride In tetrahydrofuran at 50 - 60℃; for 0.166667h; Stage #2: 2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine In tetrahydrofuran for 0.5h; | 72% |
IUPAC Name: 2,4,6,8-Tetrachloropyrimido[5,4-d]pyrimidine
Synonyms of Tetrachloropyrimido(5,4-d)pyrimidine (CAS NO.32980-71-5): Pyrimido[5,4-d]pyrimidine,2,4,6,8-tetrachloro- ; 2,4,6,8-Tetrachloropyrimido[5,4-d]pyrimidine
CAS NO: 32980-71-5
Molecular Formula: C6Cl4N4
Molecular Weight: 269.9
Molecular Structure:
EINECS: 251-318-3
H bond acceptors: 4
H bond donors: 0
Freely Rotating Bonds: 0
Polar Surface Area: 51.56 Å2
Index of Refraction: 1.704
Molar Refractivity: 56.04 cm3
Molar Volume: 144.2 cm3
Surface Tension: 79.8 dyne/cm
Density: 1.871 g/cm3
Flash Point: 186.8 °C
Enthalpy of Vaporization: 55.53 kJ/mol
Boiling Point: 335.1 °C at 760 mmHg
Vapour Pressure: 0.000237 mmHg at 25°C
SMILES: Clc2nc(Cl)nc1c2nc(Cl)nc1Cl
InChI: InChI=1/C6Cl4N4/c7-3-1-2(12-6(10)13-3)4(8)14-5(9)11-1
InChIKey: QNKFHUMDHRWWES-UHFFFAOYA
Std. InChI: InChI=1S/C6Cl4N4/c7-3-1-2(12-6(10)13-3)4(8)14-5(9)11-1
Std. InChIKey: QNKFHUMDHRWWES-UHFFFAOYSA-N
Safety Information about Tetrachloropyrimido(5,4-d)pyrimidine (CAS NO.32980-71-5):
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
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